The synthesis and NMR investigation on novel boron derivatives of stavudine

Ruman, Tomasz; Długopolska, Karolina; Jurkiewicz, Agata; Rydel, Katarzyna; Leś, Andrzej; Rode, Wojciech

doi:10.1016/j.bioorg.2009.12.005

Cited by 3 publications

(1 citation statement)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There are many interesting questions on boron analogous of uracil nucleobase concerning, for example their relative stability order, electronic structure, chemical properties and base‐pairing ability to adenine nucleobase. In an attempt to answer these questions, density functional theory (DFT) and second‐order Møller–Plesset (MP2) computational methods in conjunction with 6‐311++ G (d,p) atomic basis set were chosen to study two boron analogues of uracil, which were recently synthesized by Ruman et al . (Scheme ) in gas phase and aqueous solution by adopting integral equation formalism of the polarized continuum model (IEF‐PCM).…”

Section: Introductionmentioning

confidence: 99%

What roles do boron substitutions play in structural, tautomeric, base pairing and electronic properties of uracil? NBO & AIM analysis

Tehrani

Abedin

Shakourian‐Fard

et al. 2012

J of Physical Organic Chem

View full text Add to dashboard Cite

The synthesis of modified versions of deoxyribonucleic acid is an area that is receiving much attention. The replacement of the nitrogen atom on the nucleobases with boron atom has provided insight into deoxyribonucleic acid and ribonucleic acid stability, recognition, and replication at the atomic level. In the present research, we investigated a detailed density functional theory study of the structural, tautomeric, base-pairing ability, bond dissociation energy, and electronic properties of two boron analogues (i.e., boron substitutions at 4-position and 5-position of uracil) of uracil nucleobase. The effects of these modifications on theirs acid-base properties have been considered. Our goal is to gather data to help elucidate the structure and electronic properties of boron analogues of uracil. Density functional theory calculations were performed using a nonlocal hybrid B3LYP and 6-311++G (d,p) atomic basis set. The result of calculation revealed that the canonical 'keto' form is the most stable tautomeric form of uracil nucleobase and its boronated analogues in the gas phase at density functional theory and second-order Møller-Plesset levels. Hyperconjugation stabilization factors that affect the stability of generated radicals and anions in these molecules were investigated by natural bond orbital analysis. Furthermore, quantum theory of atoms in molecules analysis was performed to extract the bond critical point properties of various base pairs. The electron density can be considered as a good description of the strength of the different types of hydrogen bonding.

show abstract

Section: Introductionmentioning

confidence: 99%

What roles do boron substitutions play in structural, tautomeric, base pairing and electronic properties of uracil? NBO & AIM analysis

Tehrani

Abedin

Shakourian‐Fard

et al. 2012

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

Visible Light‐Induced Decarboxylative Alkylation of Heterocyclic Aromatics with Carboxylic Acids via Anthocyanin as a Photocatalyst

Guo

Zuo

Tian

et al. 2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

A visible light‐induced decarboxylative alkylation of heterocyclic aromatics with aliphatic carboxylic acids was developed by using anthocyanins as a photocatalyst under mild conditions. A series of alkylated heterocyclic compounds were obtained in moderate to good yields by using the metal‐free decarboxylative coupling reaction under blue light. This strategy uses cheap and readily available carboxylic acids as alkylation reagents with good functional group tolerance and environmental friendliness. It is worth noting that this is the first time that anthocyanin has been used to catalyze the Minisci‐type C−H alkylation. The mechanism of decarboxylation alkylation was studied by capturing the adduct of alkyl radical and hydroquinone, thus confirming a radical mechanism. This protocol provides an alternative visible light‐induced decarboxylative alkylation for the functionalization of heterocyclic aromatics.

show abstract

Vibrational spectroscopic studies on 2′-3′-didehydro-2′-3′-dideoxythymidine using density functional theory method

Ramkumaar¹,

Srinivasan

Bhoopathy³

et al. 2014

Journal of Molecular Structure

View full text Add to dashboard Cite

The synthesis and NMR investigation on novel boron derivatives of stavudine

Cited by 3 publications

References 18 publications

What roles do boron substitutions play in structural, tautomeric, base pairing and electronic properties of uracil? NBO & AIM analysis

What roles do boron substitutions play in structural, tautomeric, base pairing and electronic properties of uracil? NBO & AIM analysis

Visible Light‐Induced Decarboxylative Alkylation of Heterocyclic Aromatics with Carboxylic Acids via Anthocyanin as a Photocatalyst

Vibrational spectroscopic studies on 2′-3′-didehydro-2′-3′-dideoxythymidine using density functional theory method

Contact Info

Product

Resources

About